149716-72-3

Usage

Uses

Used in Pharmaceutical Industry:
(1R,2R,3S,5R)-Pinanediol Pyrrolidine-2R-boronate Hydrochloride is used as an intermediate in the synthesis of prolineboronate esters, which are important for the development of pharmaceutical compounds. These esters can be utilized in the creation of novel drugs with potential therapeutic applications, such as those targeting specific enzymes or receptors in the treatment of various diseases.
Used in Chemical Research:
In the field of chemical research, (1R,2R,3S,5R)-Pinanediol Pyrrolidine-2R-boronate Hydrochloride can serve as a valuable compound for studying the effects of chirality on molecular interactions and reactivity. Its unique structure allows researchers to explore the implications of stereochemistry in chemical reactions and develop a deeper understanding of the underlying principles governing these processes.
Used in Material Science:
The specific structural features of (1R,2R,3S,5R)-Pinanediol Pyrrolidine-2R-boronate Hydrochloride may also find applications in material science, where it could be used to develop new materials with tailored properties. For example, its chiral nature could be exploited to create materials with enhanced selectivity or specificity in various applications, such as sensors, catalysts, or drug delivery systems.

Upstream product

• 7647-01-0 hydrogenchloride 
• 205116-75-2 (1S,2S,3R,5S)-pinane-2,3-diyl (N-(1,1-dimethylethoxycarbonyl)pyrrolidin-2-yl)boronate 
• 230299-05-5 bis-(+)-pinanediolato diboron 
• 1536530-89-8 C₁₈H₃₂BNO₃S 
• 1536530-69-4 C₁₈H₃₃BClNO₃S 
• 18680-27-8 pinanediol 

Relevant academic research and scientific papers

A practical synthesis of L-valyl-pyrrolidine-(2R)-boronic acid: Efficient recycling of the costly chiral auxiliary (+)-pinanediol

A practical synthesis of L-valyl-pyrrolidine-(2R)-boronic acid (1) is detailed. A previously disclosed synthesis of 1 (Snow, R.; Kelly, T. R.; Adams, J.; Coutts, S.; Perry, C. (Boehringer Ingelheim Pharmaceuticals, Inc.). WO 93/10127, 1993) was significantly improved by developing an efficient process for recycling the costly chiral auxiliary (+)- pinanediol.

Preparation method of dipeptide valine boron proline salt

The invention provides a preparation method of dipeptide valine boron proline salt. According to the preparation method, pyrrolidine boric acid with protected R groups and valine with protected R groups are used as initial raw materials, and the problem of product loss caused by complex post-treatment during deprotection is avoided, so that the yield of a target product is greatly improved,and mass production is facilitated. Through a resolution method by adopting a resolution agent, the problem of excessive loss of a product with a target configuration due to use of resolution methodswith different solubilities is avoided, so that the yield of the product with the target configuration is greatly improved.

Proline boric acid compound and preparation method and applications thereof

The invention provides a compound whose structure is shown as a formula (I) or a salt thereof. The compound is a proline boric acid proteasome inhibitor compound, and has good proteasome inhibitory activity and excellent druggability. The structural formula of the compound is shown as the formula (I).

Synthesis and biological activity of peptide proline-boronic acids as proteasome inhibitors

On the basis of the application of proline-boronic acid as pharmacophore in the kinase inhibitors and our previous research results, using proline-boronic acid as warhead, two series of peptide proline-boronic acids, dipeptide proline-boronic acids (I) and tripeptide proline-boronic acids (II), were designed and synthesized. All the synthesized compounds were first evaluated for their biological activity against MGC803 cell, and then, the best compound II-7 was selected to test its anti-tumor spectrum on six human tumor cell lines and proteasome inhibition against three subunits. The results indicated that series II have much better biological activities than series I. The compound II-7 exhibited not only excellent biological activities with IC50 values of nM level in both cell and proteasome models, but also much better subunit selectivity. Thus, proline-boronic acid as warhead is reasonable in the design of proteasome inhibitors.

Asymmetric synthesis of stable α-aminoboronic esters catalyzed by N-heterocylic carbene and copper(i) chloride

Bis(pinanediolato)diboron (B2pnd2) was used as the nucleophile instead of bis(pinacolato)diboron in the stereospecific synthesis of α-aminoboronic esters catalysed by a triazole-based N-hetereocyclic carbene (NHC) and Cu(i) chloride.

HETEROCYCLIC BORONIC ACID COMPOUNDS

Dipeptidyl peptidase IV (DPP-IV)-inhibiting compounds are provided that have formula I: wherein n is 1 to 3; X is CH2; S; O; CF2 or C (CH3)2; Z is H; halogen; hydroxyl; (C1-6)alkoxy; (C1-12)alkyl; (C3-12)cycloalkyl; phenyl; or heteroaryl; where the phenyl and heteroaryl groups are optionally mono- or independently plurisubstituted with R7; optionally, X together with an adjacent ring carbon and Z form a fused cyclopropyl; and optionally, one of the bonds in the ring containing X is a double bond; and CriRii, R1, R1, R3, R4 and R5 are as described herein. Methods for preparing these compounds, and methods for treating diabetes, especially Type II diabetes, and other related diseases are described using the compounds of formula I in pharmaceutical compositions which contain these compounds. Pharmaceutical compositions which contain combinations of these compounds with other antidiabetic agents are also described herein.